N. N. Sergeeva, V. Pablo Lopez, M. O. Senge, Synthesis of porphyryl boronates with (un)saturated side chains, Journal of Organometallic Chemistry, 693, 15, 2008, 2637 - 2640
Journal of Organometallic Chemistry 693 15
Porphyrins with (un)saturated side–chains containing boron residues were developed as synthons for porphyrin functionalization. Porphyrins with mono and bis-substituted unsaturated boronyl residues were prepared in good yields (52–66 %) using a cross–metathesis approach in the presence of Grubbs I-generation catalysts. In all cases complete E–stereoselectivity (100 %) was observed. Furthermore, formal cross–metathesis products with α,β–unsaturated chains smoothly underwent addition with bis(pinacolato)diboron [(Me4C2O2)B–B(O2C2Me4)] to yield the corresponding saturated boron compounds in 6070 % yields.
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